AU2012263504B2 - Method for producing acrylamide - Google Patents

Method for producing acrylamide Download PDF

Info

Publication number: AU2012263504B2
Authority: AU; Australia
Prior art keywords: reaction; temperature; reactor; acrylamide; acrylonitrile
Prior art date: 2011-05-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

AU2012263504A

Other languages

English (en)

Other versions

AU2012263504A1 (en

Inventor

Makoto Kanou

Kiyonobu Niwa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2011-05-31

Filing date

2012-05-29

Publication date

2015-10-01

2012-05-29 Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp

2013-12-12 Publication of AU2012263504A1 publication Critical patent/AU2012263504A1/en

2015-10-01 Application granted granted Critical

2015-10-01 Publication of AU2012263504B2 publication Critical patent/AU2012263504B2/en

2018-01-04 Assigned to MITSUBISHI CHEMICAL CORPORATION reassignment MITSUBISHI CHEMICAL CORPORATION Request for Assignment Assignors: MITSUBISHI RAYON CO., LTD.

Status Active legal-status Critical Current

2032-05-29 Anticipated expiration legal-status Critical

Links

HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 79
238000004519 manufacturing process Methods 0.000 title abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 154
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
239000002994 raw material Substances 0.000 claims description 50
239000000463 material Substances 0.000 claims description 2
241000011102 Thera Species 0.000 claims 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 64
238000007710 freezing Methods 0.000 abstract description 17
230000008014 freezing Effects 0.000 abstract description 17
230000000887 hydrating effect Effects 0.000 abstract description 14
238000006703 hydration reaction Methods 0.000 abstract description 10
239000003054 catalyst Substances 0.000 abstract description 5
239000007858 starting material Substances 0.000 abstract 2
108090000790 Enzymes Proteins 0.000 description 37
102000004190 Enzymes Human genes 0.000 description 37
238000000034 method Methods 0.000 description 33
239000011942 biocatalyst Substances 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 20
239000000498 cooling water Substances 0.000 description 17
239000000243 solution Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
210000004027 cell Anatomy 0.000 description 12
230000000977 initiatory effect Effects 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
-1 amide compound Chemical class 0.000 description 9
230000001580 bacterial effect Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 8
244000005700 microbiome Species 0.000 description 8
239000012159 carrier gas Substances 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
230000036571 hydration Effects 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000008363 phosphate buffer Substances 0.000 description 7
239000003643 water by type Substances 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
108010024026 Nitrile hydratase Proteins 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
210000004102 animal cell Anatomy 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000006285 cell suspension Substances 0.000 description 3
210000003463 organelle Anatomy 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000011144 upstream manufacturing Methods 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000590020 Achromobacter Species 0.000 description 1
241000589291 Acinetobacter Species 0.000 description 1
241000607534 Aeromonas Species 0.000 description 1
241000478345 Afer Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000589158 Agrobacterium Species 0.000 description 1
BMFMQGXDDJALKQ-BYPYZUCNSA-N Argininic acid Chemical compound NC(N)=NCCC[C@H](O)C(O)=O BMFMQGXDDJALKQ-BYPYZUCNSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000588923 Citrobacter Species 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000588698 Erwinia Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
241000192041 Micrococcus Species 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
241001296096 Probles Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000187603 Pseudonocardia Species 0.000 description 1
241000589180 Rhizobium Species 0.000 description 1
241000316848 Rhodococcus <scale insect> Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
241000589506 Xanthobacter Species 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005597 polymer membrane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ZNVGYHOBTCWGTO-UHFFFAOYSA-N solutin Natural products Cc1cc(O)cc2OC(C)(O)C(=O)c12 ZNVGYHOBTCWGTO-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Biotechnology (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

AU2012263504A 2011-05-31 2012-05-29 Method for producing acrylamide Active AU2012263504B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2011121849		2011-05-31
JP2011-121849		2011-05-31
PCT/JP2012/063728 WO2012165415A1 (ja)	2011-05-31	2012-05-29	アクリルアミドの製造方法

Publications (2)

Publication Number	Publication Date
AU2012263504A1 AU2012263504A1 (en)	2013-12-12
AU2012263504B2 true AU2012263504B2 (en)	2015-10-01

Family

ID=47259269

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2012263504A Active AU2012263504B2 (en)	2011-05-31	2012-05-29	Method for producing acrylamide

Country Status (7)

Country	Link
US (1)	US9181569B2 (zh)
EP (1)	EP2716765B1 (zh)
JP (1)	JPWO2012165415A1 (zh)
KR (1)	KR101975068B1 (zh)
CN (2)	CN103687956A (zh)
AU (1)	AU2012263504B2 (zh)
WO (1)	WO2012165415A1 (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2930243B1 (en) *	2012-12-10	2020-12-23	Mitsubishi Chemical Corporation	Method for producing acrylamide
WO2016006556A1 (ja)	2014-07-10	2016-01-14	三菱レイヨン株式会社	化合物の製造方法及び前記製造方法に用いられる化合物の製造システム
EP3225693A1 (en) *	2016-03-29	2017-10-04	Basf Se	Method for preparing aqueous acrylamide solutions
WO2019097123A1 (en) *	2017-11-20	2019-05-23	Kemira Oyj	A process for producing aqueous acrylamide solution, aqueous acrylamide solution and use thereof
CA3156963A1 (en)	2019-11-05	2021-05-14	Diego GHISLIERI	Method of storing a biocatalyst

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4414331A (en) *	1979-06-19	1983-11-08	Nitto Chemical Industry Co., Ltd.	Process for producing a highly concentrated aqueous acrylamide solution by means of microorganisms

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IT1162484B (it) *	1978-03-29	1987-04-01	Nitto Chemical Industry Co Ltd	Procedimento pe produrre acrilammide o metacrilammide impiegando microorganismi
JP3344594B2 (ja)	1992-12-14	2002-11-11	新日本石油化学株式会社	反応方法
JP4672161B2 (ja)	2000-03-29	2011-04-20	三井化学株式会社	アミド化合物の製造方法
DE10120550A1 (de)	2001-04-26	2002-10-31	Stockhausen Chem Fab Gmbh	Verfahren zur Herstellung einer wässrigen Acrylamidlösung mit einem Biokatalysator
TWI312010B (en)	2001-06-22	2009-07-11	Mitsubishi Rayon Co	A producing method of using control reactive temperature of a living catalyst of chemical compound
JP5630017B2 (ja) *	2008-03-14	2014-11-26	三菱レイヨン株式会社	アミド化合物の製造方法
EP2336346B1 (en) *	2008-10-03	2016-12-07	Dia-Nitrix Co., Ltd.	Method for producing acrylamide
JP6098509B2 (ja) *	2011-05-19	2017-03-22	三菱レイヨン株式会社	アクリルアミド水溶液の製造方法

2012
- 2012-05-29 JP JP2013518094A patent/JPWO2012165415A1/ja active Pending
- 2012-05-29 KR KR1020137030745A patent/KR101975068B1/ko active IP Right Grant
- 2012-05-29 WO PCT/JP2012/063728 patent/WO2012165415A1/ja active Application Filing
- 2012-05-29 CN CN201280027002.9A patent/CN103687956A/zh active Pending
- 2012-05-29 US US14/122,052 patent/US9181569B2/en active Active
- 2012-05-29 EP EP12794114.4A patent/EP2716765B1/en active Active
- 2012-05-29 CN CN201710672127.1A patent/CN107267565A/zh active Pending
- 2012-05-29 AU AU2012263504A patent/AU2012263504B2/en active Active

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4414331A (en) *	1979-06-19	1983-11-08	Nitto Chemical Industry Co., Ltd.	Process for producing a highly concentrated aqueous acrylamide solution by means of microorganisms

Also Published As

Publication number	Publication date
US9181569B2 (en)	2015-11-10
WO2012165415A1 (ja)	2012-12-06
EP2716765A4 (en)	2014-11-26
CN107267565A (zh)	2017-10-20
KR20140039197A (ko)	2014-04-01
EP2716765B1 (en)	2022-06-15
JPWO2012165415A1 (ja)	2015-02-23
EP2716765A1 (en)	2014-04-09
KR101975068B1 (ko)	2019-05-03
CN103687956A (zh)	2014-03-26
US20140134683A1 (en)	2014-05-15

Legal Events

Date

Code

Title

Description

2016-01-28

FGA

Letters patent sealed or granted (standard patent)

2018-01-04

PC

Assignment registered

Owner name: MITSUBISHI CHEMICAL CORPORATION

Free format text: FORMER OWNER(S): MITSUBISHI RAYON CO., LTD.

Publication	Publication Date	Title
EP2336346B1 (en)	2016-12-07	Method for producing acrylamide
AU2012263504B2 (en)	2015-10-01	Method for producing acrylamide
EP1380652B1 (en)	2010-08-25	Process for producing acrylamide using a microbial catalyst that has been washed with aqueous acrylic acid solution
EP2540700B1 (en)	2017-07-12	Stable aqueous acrylamide solution
JP4669220B2 (ja)	2011-04-13	反応温度を制御した、生体触媒を用いた化合物の製造方法
KR101878012B1 (ko)	2018-07-12	아크릴아미드 수용액의 제조 방법
KR101894617B1 (ko)	2018-09-03	아크릴아미드 수용액의 제조 방법
KR101774674B1 (ko)	2017-09-04	아크릴아미드의 제조 방법
JP5849428B2 (ja)	2016-01-27	微生物触媒を用いた化合物の製造方法
JP2004321062A (ja)	2004-11-18	生体触媒の使用方法